25580-38-5

Basic information

• Product Name: Threonine, 2-methyl- (9CI)
• Synonyms: Threonine, 2-methyl- (9CI)
• CAS NO: 25580-38-5
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.14574
• Product Categories: GLYCINESCAFFOLD
• Mol File: 25580-38-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Threonine, 2-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Threonine, 2-methyl- (9CI)(25580-38-5)
• EPA Substance Registry System: Threonine, 2-methyl- (9CI)(25580-38-5)

Safety Data

• Hazardous Substances Data: 25580-38-5(Hazardous Substances Data)

Upstream product

• 88318-70-1 (4R,5R)-4,5-dimethyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester 
• 211805-81-1 (2S,3S)-2-Azido-3-hydroxy-2-methyl-butyric acid benzyl ester 
• 152036-30-1 (2S,5S,1'S)-5-(1'-Hydroxyethyl)-3,5-dimethyl-4-oxoimidazolidin-1-carbonsaeure-t-butylester 
• 88318-69-8 (4S,5S)-4,5-Dihydro-4,5-dimethyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 43197-50-8 copper(II) alaninate 
• 75-07-0 acetaldehyde 
• 677344-58-0 (4R,1'S)-N-(tert-butoxycarbonyl)-4-(1'-hydroxyethyl)-2,2,4-trimethyloxazolidine 
• 37526-88-8 benzyl tiglate 
• 677344-57-9 (1S,7aS)-1,5,5,7a-tetramethyl-2,6-dioxa-4-azapentalen-3-one 
• 677344-50-2 (1R,7aS)-1,5,5,7a-tetramethyl-2,6-dioxa-4-azapentalen-3-one 
• 677344-64-8 (4S,5R)-4-(hydroxymethyl)-4,5-dimethyloxazolidin-2-one 
• 677344-61-5 (1R,7aR)-1,5,5,7a-tetramethyl-2,6-dioxa-4-azapentalen-3-one 
• 677344-59-1 (1S,7aR)-1,5,5,7a-tetramethyl-2,6-dioxa-4-azapentalen-3-one 

Relevant articles and documents

Biocatalytic access to α,α-dialkyl-α-amino acids by a mechanism-based approach

(figure presented) New donors - new products: Threonine aldolases (L-TA, D-TA) have now been found to accept donors other than glycine. In a simple asymmetric biocatalytic aldol reaction alanine, serine, and cysteine reacted with a range of simple acceptor aldehydes to yielded α-substituted serine derivatives (see scheme; PLP=pyridoxal phosphate).

α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine

The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-l-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of α-methylthreonine by an α-alkylation reaction and in the synthesis of chiral α,β-dehydroamino acid derivatives, using the tandem retro-O-Michael/γ-alkylation reactions as key steps.

α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: Application in the synthesis of all stereoisomers of α- methylthreonine

The asymmetric synthesis of all stereoisomers of α-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different β-substituted α-methylserines.